Structure via PubChem · Public domain (PubChem)
calcifediol
Sign in to saveAlso known as 25-hydroxyvitamin D3, calcidiol, Calderol, U-32070E, (3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol, (3S,5Z,7E)-9,10-secocholesta-5,7,10-triene-3,25-diol, (5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol, 25-hydroxycholecalciferol
Calcifediol, also known as calcidiol, 25-hydroxycholecalciferol, or 25-hydroxyvitamin D3 (abbreviated 25(OH)D3), is a form of vitamin D produced in the liver by hydroxylation of vitamin D3 (cholecalciferol) by the enzyme vitamin D 25-hydroxylase. Calcifediol can be further hydroxylated by the enzyme 25(OH)D-1α-hydroxylase, primarily in the kidney, to form calcitriol (1,25-(OH)2D3), which is the active hormonal form of vitamin D.
In the Vinony graph
Within Vinony's link graph, calcifediol is referenced by 319 other articles, and connects out to cytochrome P450 family 2 subfamily R member 1, vitamin D and cholecalciferol.
Vinony files it under Conjugated dienes, Diols and ECHA InfoCard ID from Wikidata.
Its subject is documented across 21 Wikipedia language editions.
Chemical data
- Formula
- C27H44O2
- Molecular weight
- 400.6 g/mol
- IUPAC name
- (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
- SMILES
- C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C
- InChIKey
- JWUBBDSIWDLEOM-DTOXIADCSA-N
- XLogP
- 6.2
- Polar surface area
- 40.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1980
- Admin. routes
- oral
via ChEMBL · EBI
Research
5,097 papers- Calcifediol: Mechanisms of Action.Nutrients · 2023
- Calcifediol for Use in Treatment of Respiratory Disease.Nutrients · 2022
- Calcifediol: a review of its pharmacological characteristics and clinical use in correcting vitamin D deficiency.European journal of nutrition · 2023
- Calcifediol (25OHD) Deficiency and Its Treatment in Women's Health and Fertility.Nutrients · 2022
- [Biosynthesis of calcifediol and calcitriol: a review].Sheng wu gong cheng xue bao = Chinese journal of biotechnology · 2024
via PubMed
Wikidata facts
- Mass
- 400.334
- Has use
- medication
Show 9 more facts
- chemical formula
- C₂₇H₄₄O₂
- canonical SMILES
- CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
- World Health Organisation international non-proprietary name
- calcifediol
- found in taxon
- Solanum glaucophyllum
- isomeric SMILES
- C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)CCC3=C
- NCI Thesaurus ID
- C77155
- physically interacts with
- cytochrome P450 family 2 subfamily R member 1
- Commons category
- Calcifediol
- subject has role
- primary metabolite
Sources (8)
via Wikidata · CC0
~8 min read
Encyclopedic overview
9 sectionsContents
- Biology
- Blood test for vitamin D deficiency
- Supplementation
- Interactive pathway map
- History
- Research
- Other Organisms
- Teleost Fish
- References
{{chembox | Verifiedfields = changed | verifiedrevid = 480474501 | ImageFile = Calcidiol2.svg | ImageClass = skin-invert-image | ImageAlt = Skeletal formula of calcifediol | ImageFile1 = Calcifediol 3D ball.png | ImageClass1 = bg-transparent | ImageAlt1 = Ball-and-stick model of the calcifediol molecule | PIN = (1S,3Z)-3-[(2E)-2-{(1R,3aS,7aR)-1-[(2R)-6-Hydroxy-6-methylheptan-2-yl]-7a-methyloctahydro-4H-inden-4-ylidene}ethylidene]-4-methylidenecyclohexan-1-ol | OtherNames = 25-Hydroxyvitamin D325-HydroxycholecalciferolCalcidiol |Section1= |Section2= | Section6 = |Section7= }} Calcifediol, also known as calcidiol, 25-hydroxycholecalciferol, or 25-hydroxyvitamin D3 (abbreviated 25(OH)D3), is a form of vitamin D produced in the liver by hydroxylation of vitamin D3 (cholecalciferol) by the enzyme vitamin D 25-hydroxylase. Calcifediol can be further hydroxylated by the enzyme 25(OH)D-1α-hydroxylase, primarily in the kidney, to form calcitriol (1,25-(OH)2D3), which is the active hormonal form of vitamin D.
Calcifediol is strongly bound in blood by the vitamin D-binding protein. Measurement of serum calcifediol is the usual test performed to determine a person's vitamin D status, to show vitamin D deficiency or sufficiency. Calcifediol is available as an oral medication in some countries to supplement vitamin D status.
Excerpted from Wikipedia’s “calcifediol” article, available under the CC BY-SA 4.0 licence.